EP0150748A1 - Dérivés d'acyloxythiophènes - Google Patents

Dérivés d'acyloxythiophènes Download PDF

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Publication number
EP0150748A1
EP0150748A1 EP85100293A EP85100293A EP0150748A1 EP 0150748 A1 EP0150748 A1 EP 0150748A1 EP 85100293 A EP85100293 A EP 85100293A EP 85100293 A EP85100293 A EP 85100293A EP 0150748 A1 EP0150748 A1 EP 0150748A1
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EP
European Patent Office
Prior art keywords
fluorine
carbon atoms
chlorine
trifluoromethyl
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP85100293A
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German (de)
English (en)
Other versions
EP0150748B1 (en
Inventor
Werner Dr. Daum
Erich Dr. Klauke
Engelbert Dr. Kühle
Wilhelm Dr. Brandes
Paul Dr. Reinecke
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Priority to AT85100293T priority Critical patent/ATE57926T1/de
Publication of EP0150748A1 publication Critical patent/EP0150748A1/fr
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Publication of EP0150748B1 publication Critical patent/EP0150748B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing >N—S—C≡(Hal)3 groups

Definitions

  • the present invention relates to new acyloxythiophene derivatives, a process for their preparation and their use as crop protection agents, especially as fungicides.
  • thiophene derivatives such as, for example, 2,5-bis (butoxycarbonyl) -3-methyl-4-styrylcarbonyloxy-thiophene and 2,5-bis-ethoxycarbonyl-3,4-bis-benzoyloxy- have thiophene and fungicidal properties (cf. EP 93 384 and EP 32 748).
  • the new acyloxythiophene derivatives of the formula (I) have fungicidal properties.
  • the acyloxythiophene derivatives of the formula (I) according to the invention show a better fungicidal activity than the fungicides known from the prior art, such as. B. 2,5-bis (isopropoxycarbonyl) -3-methyl-4- (3-methylbenzoyloxy) thiophene, 2-sec-butyl-4,6-dimitrophenyl-3-methylcrotonate and J or 6-methyl-2 -oxo-1,3-dithiolo- [4,5-b] quinoxaline.
  • connections e.g. are produced from fluorocarbonyl-N- (trifluoromethyl-sulfenyl) anilines and formic acid in the temperature range between 50 ° C and 100 ° C (cf. DE-OS 1 810 580 or the corresponding GB-PS 1 229 083, DAS 1 293 754 or FR-PS 1 524 722).
  • Suitable diluents for the process are all organic solvents which are inert to the reactants; polar solvents are preferably used. Examples include acetonitrile, acetone, chloroform, benzonitrile, dimethylacetamide, dimethylformamide, dimethyl sulfoxide, chlorobenzene, ethyl acetate, dioxane, methyl ethyl ketone, methylene chloride and tetrahydrofuran.
  • the reactions can also be carried out in heterogeneous systems consisting of water and a water-immiscible solvent.
  • Organic bases preferably tertiary amines, are used as acid binders for the reaction. These include: quinoline, dimethylbenzylamine, dimethylaniline, ethyldicyclohexylamine, ethyldiisopropylamine, picoline, pyridine and triethylamine.
  • Preferred water-binding agents when using carboxylic acids are carbodiimides, such as Dicyclohexylcarbodiimide used.
  • reaction temperatures and the reaction time are determined by the activity of the starting products. In general, about -50 to + 80 ° C, preferably between -10 and + 60 ° C.
  • alkali metal or alkaline earth metal salts of the thiophene derivative to be reacted can be initially introduced in an inert solvent, or the salt can be produced by adding alkali metal hydroxide solution, alcoholates or a corresponding alkaline earth metal compound to a mixture of the thiophene derivative and a high-boiling solvent and then carefully dewatered or the alcohol distilled off or an alkali or alkaline earth hydride is added.
  • the active compounds according to the invention precipitate in crystalline form or remain dissolved in the organic solvent and can then be separated out after washing out the solution with water by carefully concentrating the solution or by adding less polar organic solvents, such as cyclohexane, dibutyl ether or carbon tetrachloride. If necessary, water-miscible polar solvents must be removed by evaporation in vacuo after the reaction.
  • the compounds according to the invention are dissolved in a water-miscible solvent, they can also be precipitated by adding water.
  • the compounds according to the invention partly decompose at a higher temperature; in these cases the melting points can only be determined with little accuracy or not at all.
  • the presence of certain structural elements can be seen from the NMR spectra.
  • the active compounds according to the invention have a strong microbicidal action and can be used practically to combat unwanted microorganisms.
  • the active ingredients are suitable for use as crop protection agents, in particular as fungicides.
  • Fungicidal agents in crop protection are used to control Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidionycetes, Deuteromycetes.
  • Bactericidal agents are e.g. used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV formulations.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • water e.g. organic solvents can also be used as auxiliary solvents.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethyl formanide and dimethyl sulfoxide, and water.
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and pressure, e.g. Aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
  • Possible solid carriers are: e.g. natural rock meals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock meals, such as highly disperse silica, aluminum oxide and silicates. The following are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice,
  • Possible emulsifying and / or foam-generating agents are: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ether, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and tietall phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and tietall phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can be present in the formulations in a mixture with other known active compounds, such as other fungicides, insecticides, acaricides, and also in mixtures with fertilizers and growth regulators.
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, foams, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume process or to inject the active ingredient preparation or the active ingredient into the soil itself. The seeds of the plants can also be treated.
  • the active compound concentrations in the use forms can be varied within a substantial range. They are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001%.
  • amounts of active ingredient of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.
  • active ingredient concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02%, are required at the site of action.
  • the starting compounds of formula (II) can e.g. are manufactured as follows:
  • the starting compounds of the formula (III) can be prepared in accordance with the instructions described in EP 93 384 and DAS 10 20 641. The following connections are new: Melting point: 123.5 ° C (from diethyl ketone) Melting point: 75 ° C (from acetonitrile)
  • Solvent 4.7 parts by weight of acetone emulsifier: 0.3 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in a greenhouse at 23 to 24 ° C and at a relative humidity of approx. 75%.
  • Evaluation is carried out 10 days after the inoculation.
  • Solvent 4.7 parts by weight of acetone emulsifier: 0.3 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in a greenhouse at 23 ° C. and a relative humidity of approx. 70%.
  • Evaluation is carried out 9 days after the inoculation.
  • Solvent 100 parts by weight of dimethylformamide emulsifier: 0.25 part by weight of alkylaryl polyglyco-ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • the plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80%.
  • Evaluation is carried out 7 days after the inoculation.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
EP85100293A 1984-01-26 1985-01-14 Acyloxytiophene derivatives Expired - Lifetime EP0150748B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT85100293T ATE57926T1 (de) 1984-01-26 1985-01-14 Acyloxythiophen-derivate.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3402625 1984-01-26
DE19843402625 DE3402625A1 (de) 1984-01-26 1984-01-26 Acyloxythiophen-derivate

Publications (2)

Publication Number Publication Date
EP0150748A1 true EP0150748A1 (fr) 1985-08-07
EP0150748B1 EP0150748B1 (en) 1990-10-31

Family

ID=6225956

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85100293A Expired - Lifetime EP0150748B1 (en) 1984-01-26 1985-01-14 Acyloxytiophene derivatives

Country Status (16)

Country Link
US (1) US4914123A (fr)
EP (1) EP0150748B1 (fr)
JP (1) JPS60163879A (fr)
KR (1) KR850005430A (fr)
AT (1) ATE57926T1 (fr)
AU (1) AU3811485A (fr)
BR (1) BR8500301A (fr)
DE (1) DE3402625A1 (fr)
DK (1) DK36585A (fr)
ES (1) ES8601961A1 (fr)
GR (1) GR850225B (fr)
HU (1) HUT36822A (fr)
IL (1) IL74137A0 (fr)
NZ (1) NZ210911A (fr)
PT (1) PT79832B (fr)
ZA (1) ZA85611B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0243776A3 (fr) * 1986-04-24 1989-09-20 Bayer Ag Dérivés de carbamoyloxythiophène

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4876462B2 (ja) * 2005-07-12 2012-02-15 ソニー株式会社 画像表示装置

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0093384A1 (fr) * 1982-04-30 1983-11-09 Ube Industries, Ltd. Dérivés de thiophène et composition fongicide les contenant

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6058918B2 (ja) * 1980-01-22 1985-12-23 宇部興産株式会社 チオフエン誘導体および農園芸用殺菌剤
US4421761A (en) * 1981-01-27 1983-12-20 Hokko Chemical Industry Co. Ltd. Thiophene derivatives

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0093384A1 (fr) * 1982-04-30 1983-11-09 Ube Industries, Ltd. Dérivés de thiophène et composition fongicide les contenant

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0243776A3 (fr) * 1986-04-24 1989-09-20 Bayer Ag Dérivés de carbamoyloxythiophène

Also Published As

Publication number Publication date
PT79832A (en) 1985-02-01
DK36585D0 (da) 1985-01-25
JPS60163879A (ja) 1985-08-26
AU3811485A (en) 1985-08-01
ES539858A0 (es) 1985-11-16
NZ210911A (en) 1987-09-30
DE3402625A1 (de) 1985-08-01
DK36585A (da) 1985-07-27
IL74137A0 (en) 1985-04-30
PT79832B (en) 1986-12-18
BR8500301A (pt) 1985-09-03
KR850005430A (ko) 1985-08-26
EP0150748B1 (en) 1990-10-31
ES8601961A1 (es) 1985-11-16
ATE57926T1 (de) 1990-11-15
GR850225B (fr) 1985-05-24
ZA85611B (en) 1985-09-25
US4914123A (en) 1990-04-03
HUT36822A (en) 1985-10-28

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